Reaktion #1889736

Reaktionsgleichung

8-(tert-butoxycarbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid

EDC

HOBt

phenethylamine

DMF

→

N-(2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide

8-(5-{[(4-Aminobiphenyl-3-yl)amino]carbonyl}pyridin-2-yl)-N-(2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with H2O (1×5 mL) and brine (1×5 mL)
2. 2
   TrocknenThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   workup.ADDITIONtreated with TFA (2 mL)
6. 6
   EinengenThe reaction mixture was concentrated
7. 7
   Sonstigethe crude oil purified by reverse-phase chromatography (10-75% MeCN/H2O with 0.05% TFA)

Vorschrift

To a solution of 8-(tert-butoxycarbonyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid (300 mg, 1.06 mmol), EDC (242 mg, 1.26 mmol), HOBt (171 mg, 1.26 mmol) in DMF (4 mL) was added phenethylamine (159 μL, 1.26 mmol). After 4 h at room temperature, the reaction mixture was diluted with EtOAc (10 mL) and washed with H2O (1×5 mL) and brine (1×5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The crude oil was taken up in CH2Cl2 (4 mL) and treated with TFA (2 mL). The reaction mixture was concentrated and the crude oil purified by reverse-phase chromatography (10-75% MeCN/H2O with 0.05% TFA) to give the N-(2-phenylethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxamide confirmed by MS (ESI+): cal'd [M+H]+ 288.2, obs'd 288.2.

Quelle